1. Field of the Invention
This invention concerns the preparation of the bis-urethan of 1,3-Diamino-2,4,6-trinitrobenzene (DATB) [I] and the preparation of DATB [II] from its bis-urethan. ##STR1##
2. Background References
The following articles are cited as reference materials to the prior art of this invention:
(1) Noelting and Collin--Berichte der Deutschen Chemischen Gesellschaft, Vol. 17, 260 (1884). PA0 (2) Barr--Berichte der Deutschen Chemischen Gesellschaft, Vol. 21, 1546 (1888). PA0 (3) Blanksma--Recueil des Travaux chimiques des Pay-Bas, Vol. 21, 324 (1902). PA0 (4) Meisenheimer and Patzig--Berichte der Deutschen Chemischen Gesellschaft, Vol. 39, 2540 (1906). PA0 (5) Blanksma--Recueil des Travaux chimiques des Pay-Bas, Vol. 27, 56 (1908). PA0 (6) Korner and Contardi--Atti della Reale Academia dei Lincei (Rendiconti) [5] Vol. 17, 473 (1908). PA0 (7) Korner and Contardi--Atti della Reale Academia dei Lincei (Rendiconti) [5] Vol. 18, 101 (1909). PA0 (8) Hass, Feuer, and Harban--Journal of The American Chemical Society, Vol. 72 pp 2282-3 (1950). PA0 (9) Feuer and Harban--U.S. Pat. No. 2,679,538; May 25, 1954. PA0 (10) Warman and Siele--Journal of Organic Chemistry, Vol. 26, pp. 2997-8 (1961). PA0 (11) Orlova, Zhilin, Zbarskii, Maksimov, and Shutov--Russian Pat. No. 147,119; Apr. 28, 1962. PA0 (12) Siele and Warman--Journal of Organic Chemistry, Vol. 27, pp. 1910-11, (1962). PA0 (13) Shutov, Zhilin, Zbarskii, and Orlova--Russian Pat. No. 169,504; Mar. 17, 1965. PA0 (14) Hoffman and McDonough--U.S. Pat. No. 3,278,604; Oct. 11, 1966. PA0 (15) Dacons, Kamlet and Hoffsommer--U.S. Pat. No. 3,394,183; July 23, 1968. PA0 (16) Lorang--Receil des Travaux chimiques des Pay-bas, Vol. 46, pp. 635-52, (1927).
3. Description of the Prior Art
The prior art teaches that given suitable substitution in the one and three positions of a 2,4,6-trinitrobenzene derivative, the compound will react with ammonia gas or alcoholic ammonia to replace the substituents in the one and three positions with the--NH.sub.2 groups, giving the explosive, DATB, in Equation (1). ##STR2##
In Equation (1), X and Y may be halogens or ethers or a mixture (i.e.--X may be a halogen and Y an ether.) This is the teaching of references 1 thru 15, save only reference 4. This Equation (1) in one or another of its variations is the common route by which the explosive DATB is prepared.
Reference (4) presents the curious reaction of Equation (2). ##STR3##
Intuitively, one would not expect a high yield of DATB from Equation (2). As previously mentioned, references 1 thru 15 have the three nitro groups in place on the benzene ring before the amino groups (NH.sub.2) are introduced. Only reference 16 reverses this procedure. In reference 16, Lorang studied the reactions of polynitroaromatic N-nitroureas, such as [III] which he made by equation (3). ##STR4## Note that [III] is not only a polynitroaromatic compound, but it is also a double nitramine and would be expected to be somewhat hazardous. Lorang heated [III] with H.sub.2 O and obtained DATB; he also heated [III] with alcohol to make the bis-urethan of DATB [I] as in equation (4): ##STR5## Lorang then reacted (I) with alcoholic ammonia to make 1,3-Diamino-2,4,6-trinitrobenzene (DATB).